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How to Travel from

Chicago to Winnipeg

by Plane, Rideshare, Route or Car

Chicago
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Winnipeg
Transport search to Winnipeg
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A and B, and we will create
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United States of America Canada Chicago Winnipeg
Chicago
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Winnipeg
Building a composite car route
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A and B, and we will create
a convenient route for you 👍
To build a composite route, click the "Add point" button.
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Cheapest
Best Offer!
Car
14 h 19 min
1387 km.
from $76
Composite Route Car Only

Nine ways to Travel from Chicago to Winnipeg

Select an Option Below to Start Your Journey
Cheapest
By car (1 387 km)
14 h 19 min
1387 km.
from $76
Fastest
Plane to Winnipeg
Select a ticket
Other
Rideshare
14 h 19 min
1387 km.
from $18.09
Train via Dearborn
46 h 30 min
1152 km.
from $282.37
Train, Plane (Train to General Mitchell International Airport)
8 h 42 min
1152 km.
from $258.33
Train, Plane (Train to South Bend)
9 h 55 min
1152 km.
from $276.09
Bus, Plane
7 h 29 min
1152 km.
from $260.34
Bus, Train
2 d 1 h 9 min
1152 km.
from $272.40
Train
2 d 3 h 22 min
1152 km.
from $442.47

Transport providers

Airlines

Air Canada

Website:
aircanada.com
Plane from Chicago O'Hare International Airport to Winnipeg
Ave. Duration:
2h 30m
Frequency:
Every day
Estimated price:
$165.60–$700.62
Plane from General Mitchell International Airport to Winnipeg
Ave. Duration:
5h 13m
Frequency:
Every day
Estimated price:
$178.34–$764.32

American Airlines

Website:
aa.com/
Plane from Chicago O'Hare International Airport to Hector
Ave. Duration:
1h 58m
Frequency:
Every day
Estimated price:
$152.86–$636.93

Delta

Website:
delta.com/
Plane from Chicago O'Hare International Airport to Winnipeg
Ave. Duration:
4h 38m
Frequency:
Every day
Estimated price:
$127.39–$356.68
Plane from Midway International Airport to Winnipeg
Ave. Duration:
5h 20m
Frequency:
Every day
Estimated price:
$140.12–$382.16
Plane from General Mitchell International Airport to Winnipeg
Ave. Duration:
5h 1m
Frequency:
Every day
Estimated price:
$140.12–$369.42
Plane from South Bend to Winnipeg
Ave. Duration:
5h 28m
Frequency:
Every day
Estimated price:
$178.34–$445.85
Plane from Chicago O'Hare International Airport to Hector
Ave. Duration:
4h 7m
Frequency:
Every day
Estimated price:
$121.02–$356.68

United Airlines

Website:
united.com/
Plane from Chicago O'Hare International Airport to Winnipeg
Ave. Duration:
2h 30m
Frequency:
Every day
Estimated price:
$165.60–$700.62
Plane from General Mitchell International Airport to Winnipeg
Ave. Duration:
5h 13m
Frequency:
Every day
Estimated price:
$178.34–$764.32
Plane from South Bend to Winnipeg
Ave. Duration:
7h 13m
Frequency:
Every day
Estimated price:
$216.56–$891.70
Plane from Chicago O'Hare International Airport to Hector
Ave. Duration:
2h 13m
Frequency:
Every day
Estimated price:
$191.08–$636.93

Train operators

Amtrak

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from Chicago Union Station to Dearborn
Ave. Duration:
4h 47m
Frequency:
3 times a day
Estimated price:
$35.67–$140.12
Train from Chicago Union Station to Milwaukee
Ave. Duration:
1h 29m
Frequency:
Every 4 hours
Estimated price:
$12.74–$89.17
Train from Chicago Union Station to Buffalo
Ave. Duration:
10h 23m
Frequency:
Twice daily
Estimated price:
$61.15–$216.56

South Shore Line

Phone:
+1 219-926-5744
Website:
mysouthshoreline.com/
Train from Van Buren St. to South
Ave. Duration:
1h 58m
Frequency:
Every 2 hours
Estimated price:
$7.01–$16.56

VIA Rail

Phone:
+1 888 842-7245
Website:
viarail.ca/en
Train from Windsor to Toronto
Ave. Duration:
4h 10m
Frequency:
4 times a day
Estimated price:
$39.49–$108.28
Train from Toronto Union Station to Winnipeg
Ave. Duration:
34h 35m
Frequency:
Twice a week
Estimated price:
$165.60–$229.29
Train from Buffalo to Toronto
Ave. Duration:
4h 24m
Frequency:
Once daily
Estimated price:
$25.48–$95.54

Bus operators

Greyhound USA

Phone:
+1 214-849-8100
Email:
Website:
greyhound.com/
Bus from Chicago Bus Station to Kalamazoo
Ave. Duration:
3h 10m
Frequency:
Twice daily
Estimated price:
$11.46–$114.65
Bus from Chicago Bus Station to Detroit
Ave. Duration:
6h 10m
Frequency:
Twice daily
Estimated price:
$22.93–$178.34

Flixbus USA

Phone:
+1 (855) 626-8585
Website:
flixbus.com
Bus from Chicago Bus Station to Detroit
Ave. Duration:
7h 40m
Frequency:
Twice daily
Estimated price:
$28.02–$101.91
Bus from Detroit Bus Station to Toronto
Ave. Duration:
6h 25m
Frequency:
3 times a day
Estimated price:
$25.48–$89.17

Ontario Northland

Phone:
+1 705 472 4500
Email:
Website:
ontarionorthland.ca/en
Bus from Sault Ste Marie to Thunder
Ave. Duration:
9h 46m
Frequency:
6 times a week
Estimated price:
$89.17–$140.12
Bus from Thunder Bay to Winnipeg
Ave. Duration:
9h 4m
Frequency:
6 times a week
Estimated price:
$89.17–$140.12

Indian Trails

Phone:
+1 800-292-3831
Website:
indiantrails.com/
Bus from Kalamazoo, MI to St.
Ave. Duration:
8h 40m
Frequency:
Once daily
Estimated price:
$54.78–$191.08

Questions and Answers

What is the cheapest way to get from Chicago to Winnipeg?

The cheapest way to get from Chicago to Winnipeg is to drive which costs $184.78 - $282.61 and takes 14h 22m.

What is the fastest way to get from Chicago to Winnipeg?

The fastest way to get from Chicago to Winnipeg is to fly which takes 5h 46m and costs $184.78 - $456.52 .

Is there a direct train between Chicago and Winnipeg?

No, there is no direct train from Chicago station to Winnipeg. However, there are services departing from Chicago Union Station and arriving at Winnipeg via Buffalo and Toronto Union Station. The journey, including transfers, takes approximately 2 days 3h.

Is there a direct flight between Chicago and Winnipeg?

Yes, there are direct flights between Chicago and Winnipeg; these take 2h 30m and cost $184.78 - $445.65 .

How far is it from Chicago to Winnipeg?

The distance between Chicago and Winnipeg is 1175 km. The road distance is 1387.7 km.

How do I travel from Chicago to Winnipeg without a car?

The best way to get from Chicago to Winnipeg without a car is to bus and train which takes 2 days 1h and costs $173.91 - $423.91 .

How long does it take to get from Chicago to Winnipeg?

It takes approximately 5h 46m to get from Chicago to Winnipeg, including transfers.

Where do I catch the Chicago to Winnipeg train from?

Chicago to Winnipeg train services, operated by Amtrak, depart from Chicago Union Station.

Train or fly from Chicago to Winnipeg?

The best way to get from Chicago to Winnipeg is to fly which takes 5h 46m and costs $184.78 - $456.52 . Alternatively, you can train via Dearborn, which costs $206.52 - $413.04 and takes 46h 30m.

Where does the Chicago to Winnipeg train arrive?

Chicago to Winnipeg train services, operated by Amtrak, arrive at Buffalo Depew Station.

Can I drive from Chicago to Winnipeg?

Yes, the driving distance between Chicago to Winnipeg is 1388 km. It takes approximately 14h 22m to drive from Chicago to Winnipeg.

How do I get a train ticket from Chicago to Winnipeg?

Book your Chicago to Winnipeg train tickets online with Omio.

Where can I stay near Winnipeg?

There are 153+ hotels available in Winnipeg. Prices start at $46.55 per night.
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